Synthesis, asymmetric aldol reactions, and x-ray crystallography of some oxadiazinanone derivatives

Autor:	David M. Casper, Christopher G. Hamaker, Daniel M. Richmond, Jeremy F. Vaughn, Jesse A. Wolfe, Ryan A. Davis, Shawn R. Hitchcock, Stephanie L. Kuschel, Jarvis Dingle, Delvis D. Dore
Rok vydání:	2008
Předmět:	Hydrolysis chemistry.chemical_compound Aldol reaction Chemistry Organic Chemistry X-ray crystallography Substituent Propanoyl chloride Alkylation Medicinal chemistry Adduct
Zdroj:	Journal of Heterocyclic Chemistry. 45:1265-1274
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570450502
Popis:	A series of N4-substituted oxadiazinanones have been synthesized from (1R,2S)-norephedrine by a process of either reductive alkylation or arylation, N-nitrosation, reduction and cyclization. These derivatives (R = -CH2Ph, -CH2C(CH3)3, -cyclo-C6H11, -C6H5) have been acylated with propanoyl chloride and employed in the asymmetric Aldol reaction. The observed diastereoselectivities for the formation of the “non-Evans” syn-adduct ranged from 88:12 to 99:1. The hydrolysis of the Aldol adducts varied with the nature of the nitrogen substituent.
Databáze:	OpenAIRE
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